N-Iodosuccinimide-mediated dimerization and macrocyclization of indodicarbocyanine dyes

The reaction of indodicarbocyanine dyes with N-iodosuccinimide produces dimeric molecules together with the corresponding meso-iodinated dyes depending on the aryl substitution of the dyes and reaction conditions. Iodinated dyes are more reactive in BF3-catalized dimerization than brominated analogu...

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Bibliographic Details
Published in:Tetrahedron 2023-06, Vol.140, p.133485, Article 133485
Main Authors: Miltsov, Sergey, Yakimansky, Alexander, Mitroshin, Alexander, Gurzhiy, Vladislav, Alonso-Chamarro, Julian, Puyol, Mar
Format: Article
Language:English
Subjects:
bromination
Cyanine dyes
Cyclization
Dimerization
macrocyclization reactions
N-iodosuccinimide
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Summary:The reaction of indodicarbocyanine dyes with N-iodosuccinimide produces dimeric molecules together with the corresponding meso-iodinated dyes depending on the aryl substitution of the dyes and reaction conditions. Iodinated dyes are more reactive in BF3-catalized dimerization than brominated analogues. Reaction of N-iodosuccinimide with N,N′-connected dimeric pentamethines gave rise to macrocyclic dyes with 16- and 20-membered cycles. Alternartive NIS-dimerization route is less sensitive to the structure of indodicarbocyanines than NBS-dimerization route and leads to macrocyclic dyes in case of N,N′-connected dimeric pentamethines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133485